"Let's be honest. The weather here is insane," said Dewayne Callahan, owner of Callahan's Chicago Grille, a new brick-and-mortar outgrowth of his food cart business, Callahan's Chicago Dogs.
The Windy City native turned local Okie has weathered the full range of the Oklahoma City metro's temperamental climate while building his passionate side hustle into a sustainable new career. Now a 12-year resident, Callahan is well acquainted with the gamble of running an outdoor business in the state. Naturally, a kitchen ceiling is a more stable bet than an umbrella, and so far, it's paying off.
"It's great, man," Callahan said about his new location inside Automobile Alley food hall Parlor. "It's a really cool place and has a great vibe, good food, and alcoholic beverages."
Callahan's Chicago Grille nestles cozily on Parlor's second floor, neighboring pasta adventurers Bad Nonna's. A sleek new sign featuring Chicago's skyline at sunset welcomes guests to the window, and at the counter, they are free to pick up novelty paper hats that proudly bear the yellow-backed Vienna Beef logo. Callahan's exclusively uses the Chicago-based brand for its dogs.
"I've eaten many hot dogs in my life," Callahan said. "They make one of the best."
Those Vienna Beef colors adorn Callahan's cart umbrellas, too, which have caught the eyes of numerous fellow Chicagoans since he started Callahan's Chicago Dogs in 2015. While the new kitchen is a huge step up for Callahan, he plans to continue operating the two licensed carts in his stable on a seasonal, event-oriented basis. He is already booking well into 2022.
While the Callahan's Chicago Dogs name carries the banner of his core street offerings, namely Chicago dogs and Italian beef, Callahan's Chicago Grille provides an opportunity to expand his menu. His Philly cheesesteaks, offered in shaved ribeye and grilled chicken on the official menu (and sometimes in jerk chicken on his unofficial menu), have proven popular with patrons. His bone-in pork chop sandwich packs jerk flavor and melds deliciously with his grilled onions.
He also has a welcome alternative to the big-brand bagged chips from his carts in a proper menu of sides. His crinkle-cut fries are serviceable on their own but are best dressed up with the optional cheesesteak ingredients. For a less cheesy affair, go with the creamy kick that is his VooDoo Slaw.
Additionally, the Grille provides a permanent home to many of Callahan's less essential but more diverse cart offerings, which until now have fluctuated with supply and demand. His full menu of 10 dogs, brats, and sausages includes vegetarian options as well as notable street favorites like the Mac Dog, which bears macaroni and cheese with bacon.
Lunch specials are also in the works as part of Callahan's chalkboard menu, which currently fluctuates with limited-time offerings outside of the main menu. These are the "Bear Down Specials," named for the Chicago Bears football rallying cry with which Callahan grew up.
As he transforms the space into his own, Callahan is also butting against new challenges. As with any entrepreneur who has taken the leap from food truck to brick and mortar, the business hours are a jarring adjustment, and lately, this has seen him pulling back-to-back 15-hour shifts to cover gaps in staffing.
"I honestly don't have a business background. I came from health care, so it's definitely a learning experience," Callahan said, referencing the radiation therapy work that landed him in Oklahoma.
What Callahan may lack in a commercial resume, he makes up with hard work, dedication, and passion for the grill, and it's on the strength of these qualities that he climbs the learning curve. He'll still take any boost he can get, though, so he's been scouting new associates beyond his family tree, another new development for his venture.
Historically, Callahan's has been a family-run enterprise, a trait that Oklahoma Gazette highlighted in 2018 when a viral social media post brought widespread attention to the cart. That tweet was sent by Callahan's daughter, who still frequently promotes the brand online. Callahan's kids, though, are now young adults with their own dreams to forge. While his son still helps out part-time, the family business is expanding beyond the family unit.
It's fitting, then, that Callahan is now at Parlor, which in a sense is a family of kitchens of which he is now a member. Callahan has already taken to promoting the cuisine of his fellow cooks there. His friendliness is contagious.
Although he's not a born and raised Oklahoman, he could fool most. Even his cooking has a happenstance similarity to that storied tradition of Okie food, the onion burger. While he only learned of its history within the past couple of years, the grilled onions on his dogs and sandwiches are cousins in taste.
"I'd been eating [onion burgers] before I knew that connection," Callahan said. "I love grilled onions...and yes, they are great on our Maxwells."
As good as his grilled sausage-and-onion offerings are, the white onion topped Chicago dog remains Callahan's calling card. It's the best of its kind in the city. The purity of ingredients — tomato, pickle, sport pepper, relish, celery salt, poppy seed bun — stick to the classic recipe ("dragged through the garden," as Chicagoans call it). It's a style he's perfected.
His choice of Oklahoma beer to pair with his Chicago dog?
"Everything Rhymes with Orange from Roughtail Brewing," said Callahan, referring to one of the drinks Parlor offers at the upstairs bar just across from his new kitchen.
As he puts in more long shifts behind the counter, it's the more practical stakes that keep him going. Bills to pay and mouths to feed call for the daily grind, but he keeps the big picture in focus, too. He loves the way food makes people feel, and to now have his identity so wrapped into that is enough to leak the occasional moment of sentimentality.
"It's cool, man," Callahan said. "Sometimes when I come into work and look at [my name on] the sign, my heart gets a little warm."
